1,8-Diaminonaphthalene → 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride

HRID 419720

Reaction equation

HRID 419720 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH2:27][CH3:28])[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([Cl:26])[CH:20]=3)[N:18]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C1(N)C2C(=CC=CC=2N)C=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[ClH:26].[Cl:26][C:21]1[CH:20]=[C:19]([C:17]2[N:18]=[C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:15]([CH2:27][CH3:28])[CH:16]=2)[CH:24]=[CH:23][C:22]=1[F:25]

Participants

5

Reactant 3

HCID 680671,8-DiaminonaphthaleneHCID 5213051-Chloroethyl chloroformateHCID 666498541-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine

Product 1

HCID 666499424-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochlorideYield 235.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Dissolve 1-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine (263.3 mg, 1.00 equiv; 0.662 mmoles) and 1,8-Naphthalenediamine, N,N,N′,N′-Tetramethyl-(0.05 equiv, 0.033 mmoles, 7.0 mg) in 1,2-Dichloro-ethane (5 mL) and cool in an ice bath. Add 1-chloroethyl chloroformate (1.2 equiv, 0.794 mmol; 0.086 mL). Stir the reaction 10 minutes in an ice bath then heat to reflux for 20 minutes and evaporate to dryness. Dissolve the residue in methanol (5 mL) and reflux for 45 minutes and evaporate to dryness to give 268 mg (0.779 mmol, 118%) 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride.

Workup

  1. temperaturecool in an ice bath
  2. customthe reaction 10 minutes in an ice bath
  3. temperaturethen heat
  4. temperatureto reflux for 20 minutes
  5. customevaporate to dryness
  6. dissolutionDissolve the residue in methanol (5 mL)
  7. temperaturereflux for 45 minutes
  8. customevaporate to dryness

Sources & evidence

ORD record
ord-f58beba155f34212b5c2341dbd4e0be3
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Linked notes

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